Oliver Queen / Green Arrow
Earth-One / Post-Crisis / New Earth # Bonnie King was an early love interest of Oliver's. When all the Justice League members took their respective love interests to a carnival, she accompanied him (Justice League of America #7, Nov. 1961).(Justice League #7) # Dinah Lance / Black Canary - The two became an item after she joined the Justice League, and were somewhat off-and-on for years (including his brief period of being dead) before they tied that knot in 2008. New 52 # Dinah Lance /Black Canary - I assume he has the same kind of tension with Dinah in the New 52 continuity. Elseworlds / Alternate Universes Kingdom Come # DinahLance / Black Canary and Oliver are married with a daughter, the new Black Canary. Adaptations DC Animated Universe # Dinah Lance /Black Canary - Ollie initially wants to leave theJustice League after one mission, but changes his mind when he sees Black Canary. After one adventure together, the two become an item. Smallville In Smallville, Ollie and Dinah fight alongside each other, but never fall in love. When Ollie finds out that Chloe has been monitoring communication between league members, he pleads “Those e-mails between Canary and I were entirely platonic!” hinting at his desire to be with Chloe. # Lois Lane - When Oliver first moves to Metropolis and begins acting as a vigilante, it is reporter Lois Lane who gives him the name “Green Arrow Bandit,” which others shorten to “Green Arrow,” much to her chagrin. As Oliver Queen, he and Lois begin a relationship, which is complicated by his secretive lifestyle, ending in their breaking up. Later, she learns his identity as the Green Arrow and, with this out in the open, he discusses renewing their relationship, but she states that she cannot be a superhero’s girlfriend (irony).Oliver remains close to Lois and Clark as they embark on their relationship, even serving as best man at their wedding (although he botches it because he’s possessed by Darkseid) # Chloe Sullivan - In Smallville, Ollie instead has a relationship with Chloe, who is the Oracle, or the behind the-scenes tech agent, of the team of superheroes. They begin having what starts as casual sex. When Oliver believes he will die in the field, both he and Chloe confess their love for each over comms. He later begins a relationship with Chloe. The entire superhero team is later afflicted with a sort of sci-fi inebriation, causing them all to do crazy things and not remember them. Chloe and Oliver realize that they, in this time, got married, and they decide to not annul it, but remain a married couple. Years later, they have a son. Arrowverse # Laurel Lance . Black Canary '''- Olilver Queen grew up a spoiled rich kid, although he maintained a close relationship with the Lance sisters, Dinah, who in this version goes by her middle name Laurel, and Sara, who came from a middle class family. In college, Oliver dated Laurel in college, but cheated on her at least twice, first with a girl who he got pregnant and later told him she miscarried, and later with Laurel’s sister Sara. # '''Sara Lance and Oliver were on a trist together on his father’s boat when it sank and he was marooned on the island Lian Yu, believing her to be dead. # Shado - Oliver met many people on the island, including Shado, a young Chinese woman and deadly martial arts expert who had been kidnapped and taken there. After defeating her captors, Oliver lived on the island with Shado and Slade Wilson for months. Slade developed feelings for Shado, but she and Oliver became a couple. Later, it was discovered that Sara was still alive, and now on the island. The villainous Anthony Ivo put her and Shado at gunpoint, telling Oliver to choose between them. Oliver threw himself in front of Sara, and Ivo shot Shado in the head, killing her. Later, after defeating Ivo and fightin an insane Slade, Sara went into the sea again, once again presumed dead. Oliver had many more adventures before returning home. It was once insinuated that he had feelings for Taiana, a Russian girl who had also been kidnapped and taken to the island. This was complicated by the fact that Oliver had killed her brother in a fight. When she became possessed by an evil spirit, she begged Oliver to kill her, and he did so by breaking her neck. After returning home, Oliver reconnected with Laurel, and they agreed to try to be friends. 4. Helena Bertinelli / Huntress - Now a vigilante, Oliver was investigating crime boss Frank Bertinelli, and came into contact with his daughter, Helena. Helena and Oliver connected, went on a date, and had sex. He later discovered her to be the vigilante known as Huntress, out for vengeance against her father for killing her fiance. Although Oliver himself used lethal force at this point, he disapproved of her more ruthless methods, and the two came to blows before she fled. 5. McKenna - Oliver then started dating a friend of his, a police officer named McKenna. A jealous and psychotic Helena came back into town and attempted to harm McKenna before being fought off. After this, an injured McKenna left Starling City, and Oliver. 5. Felicity Smoak - Oliver recruited tech genius Felicity Smoak into his crusade at an early stage. It was soon suggested that she had feelings for him, although these were, at the time, completely one-sided. Laurel had begun dating Oliver’s best friend Tommy Merlyn, but he eventually broke it off, believing she was still in love with Oliver, and telling both they should be together. Laurel and Oliver renewed their relationship. After Tommy’s death soon after, a distraught Oliver left Starling City and Laurel, returning to Lian Yu. When Oliver returned to Starling City months later, he and Laurel again agreed to be friends. Sara then turned up, revealed to be alive, and joined Oliver as a vigilante known as The Canary. He and Sara renewed their own relationship, at first to Laurel’s chagrin, but later with her blessing. Sara later broke up with Oliver because she felt her dark personality was bad for him. Oliver then connected with, and had sex with, the CEO of his company, Isabella Roschenko, but she turned out to be an evil agent of Slade Wilson’s, out to destory him. In season 3, Oliver admits he has feeling for Felicity and asks her out on a date. That date ends with an enemy of his sending a missile into the restaurant, almost killing them both. Oliver decides a relationship with FElicity is too dangerous for her, but admits that he loves her. Later, to save his sister’s life, Oliver agrees to become Ra’s Al Ghul’s student and successor for the League of Assassins. Before he bids farewell to Felicity, the two have sex. After turning on and defeating Ra’s Al Ghul, he decides to retire from vigilante life and live with Felicity. Oliver, now in a committed relationship with Felicity, decides to return to vigilante life months later. He also discovers he has a son with Samantha Clayton, the girl he cheated on Laurel with so long ago. Samantha tells him that she will not allow him visits if he tells anyone else about the boy, William, so he keeps it a secret from Felicity. Oliver and Felicity at this time become engaged. Laurel, who had sinced joined Oliver’s crusade as The Black Canary, is killed by Damian Dahrk, admitting before she died that Oliver is the love of her life. When Felicity learns about Oliver keeping his son a secret, she breaks up with Oliver, stating that his way of keeping secrets has become too intrinsic to him (she later states it’s because he doesn’t trust her). 6. Susan Williams - After becoming mayor, Oliver starts dating reporter Susan Williams, who is also investigating his ties with the Russian mafia in his past. Oliver’s sister Thea fakes evidence that Susan reported a false story, getting her fired. Not believing that Oliver had nothing to do with it, she breaks up with him. The villain Prometheus eventually reveals to her that Oliver is the Green Arrow. Oliver sets everythg straight with her, and gets her her job back, but does not believe they should renew their relationship. After simmering tension remained between him and Felicity, the two ultimately get back together. They later decide to very quickly get married. They now live as a married couple with Oliver’s son, William, whose mother was killed earlier. Also, on Earth-X in the Arrowverse, Oliver’s doppleganger is the leader of the world Nazi government, and married to Overgirl, the doppleganger of Kara/Supergirl.